Malic acid

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H6O5
Molecular Weight	134.0874
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(CC(O)=O)C(O)=O

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C4H6O5
Molecular Weight	134.0874
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://gov.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/FR330.pdf | https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdfhttp://www.cosmeticsinfo.org/ingredient/sodium-malate | https://www.food.gov.uk/science/additives/enumberlist#h_7 | https://www.ncbi.nlm.nih.gov/pubmed/11358110 | https://www.ncbi.nlm.nih.gov/pubmed/9477166

Malic acid is a tart-tasting organic dicarboxylic acid that contributes to the taste of many sour or tart foods such as apples. Sodium Malate is the sodium salt of Malic Acid. Malic Acid and Sodium Malate can be found in a wide range of cosmetics and personal care products. Sodium Malate functions as a skin conditioning agent-humectant. As a food additive, Sodium Malate has the E number E350. Sodium Malate has demonstrated protective effect on cisplatin-induced toxicity in mice. Sodium malate could become a useful agent for the reduction of CDDP-induced toxicity, particularly nephrotoxicity and hepatotoxicity.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cisplatin-induced toxicity 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9477166 https://www.ncbi.nlm.nih.gov/pubmed/9514605	Secondary	Preclinical	Unknown Approved Use Unknown
Cardiac arrhythmia 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8974556 https://www.ncbi.nlm.nih.gov/pubmed/1458176	Preventing	Preclinical	Unknown Approved Use Unknown
Skin injuries 8 Sources: https://www.montavit.com/sites/default/files/produktdownloads/pil_acerbine_solution_06022015.pdf	Curative	Approved 8429	ACERBINE Approved Use Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.

PubMed

Title	Date	PubMed
Isocitrate dehydrogenase, malate dehydrogenase, and glutamate dehydrogenase from Archaeoglobus fulgidus.	2001	11265455
Differential gene expression in the small intestines of wildtype and W/W(V) mice.	2001 Apr	11298995
In vivo and in vitro effects of prolactin and growth hormone on lipid metabolism in a teleost, Anabas testudineus (Bloch).	2001 Apr	11290458
Crystal structure of the MJ0490 gene product of the hyperthermophilic archaebacterium Methanococcus jannaschii, a novel member of the lactate/malate family of dehydrogenases.	2001 Apr 13	11292347
Abscisic acid induces a decline in nitrogen fixation that involves leghaemoglobin, but is independent of sucrose synthase activity.	2001 Feb	11283173
High level expression of C4-specific NADP-malic enzyme in leaves and impairment of photoautotrophic growth in a C3 plant, rice.	2001 Feb	11230567
Substrate and cofactor binding to fluorescently labeled cytoplasmic malate dehydrogenase.	2001 Feb 9	11342039
NADP-malic enzyme from plants: a ubiquitous enzyme involved in different metabolic pathways.	2001 Feb 9	11172800
Reclassification of Desulfobacterium phenolicum as Desulfobacula phenolica comb. nov. and description of strain SaxT as Desulfotignum balticum gen. nov., sp. nov.	2001 Jan	11211256
Identification and characterization of T cell-stimulating antigens from Leishmania by CD4 T cell expression cloning.	2001 Jan 1	11123329
Cat8 and Sip4 mediate regulated transcriptional activation of the yeast malate dehydrogenase gene MDH2 by three carbon source-responsive promoter elements.	2001 Jan 30	11169757
Massive sequence comparisons as a help in annotating genomic sequences.	2001 Jul	11435413
Altered expression and function of mitochondrial beta-oxidation enzymes in juvenile intrauterine-growth-retarded rat skeletal muscle.	2001 Jul	11420423
Metabolic flux analysis for succinic acid production by recombinant Escherichia coli with amplified malic enzyme activity.	2001 Jul 20	11369997
Transcriptome meets metabolome: hierarchical and metabolic regulation of the glycolytic pathway.	2001 Jul 6	11445079
Tungstate Uptake by a highly specific ABC transporter in Eubacterium acidaminophilum.	2001 Jul 6	11292832
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.	2001 Jun	11405809
What controls the outer mitochondrial membrane permeability for ADP: facts for and against the role of oncotic pressure.	2001 Jun 1	11334786
The homeodomain proteins PBX and MEIS1 are accessory factors that enhance thyroid hormone regulation of the malic enzyme gene in hepatocytes.	2001 Jun 29	11331288
Effect of the herbicide glyphosate on enzymatic activity in pregnant rats and their fetuses.	2001 Mar	11237511
Methyl pyruvate initiates membrane depolarization and insulin release by metabolic factors other than ATP.	2001 Mar 1	11171113
Induction of the mitochondrial permeability transition mediates the killing of HeLa cells by staurosporine.	2001 Mar 15	11289115
Identification of the human mitochondrial oxodicarboxylate carrier. Bacterial expression, reconstitution, functional characterization, tissue distribution, and chromosomal location.	2001 Mar 16	11083877
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.	2001 May	11440113
Magnesium ameliorates aluminum rhizotoxicity in soybean by increasing citric acid production and exudation by roots.	2001 May	11382822
Comprehensive chemical profiling of gramineous plant root exudates using high-resolution NMR and MS.	2001 May	11382236
Determination of organic acids and inorganic anions in wine by isotachophoresis on a planar chip.	2001 May 4	11382288

Patents

Sample Use Guides

In Vivo Use Guide

Apply Acerbine solution (malic acid, salicylic acid, benzoic acid) to the wound or damaged skin two or more times daily or moisten the dressing again. Once scar formation begins, one application a day is generally sufficient.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:34 GMT 2023`
Record UNII	817L1N4CKP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Malic acid

Official Name

English

MALIC ACID [USP IMPURITY]

Common Name

English

MALIC ACID, DL-

Common Name

English

POMALOUS ACID

Common Name

English

INS NO.296

Code

English

MALIC ACID [VANDF]

Common Name

English

MALATE

Common Name

English

MALIC ACID [INCI]

Common Name

English

MALIC ACID [USP-RS]

Common Name

English

DL-MALIC ACID

Common Name

English

HYDROXYBUTANEDIOIC ACID, (±)-

Systematic Name

English

MALIC ACID [FCC]

Common Name

English

E-296

Code

English

NSC-25941

Code

English

INS NO. 296

Code

English

E296

Code

English

(±)-MALIC ACID

Common Name

English

MALIC ACID [II]

Common Name

English

MALIC ACID [EP MONOGRAPH]

Common Name

English

HYDROXYBUTANEDIOIC ACID [HSDB]

Common Name

English

INS-296

Code

English

MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]

Common Name

English

D,L-MALIC ACID

Common Name

English

Malic acid [WHO-DD]

Common Name

English

HYDROXYSUCCINIC ACID

Common Name

English

MALIC ACID [MI]

Common Name

English

2-HYDROXYBUTANEDIOIC ACID

Systematic Name

English

MALIC ACID [NF]

Common Name

English

Classification Tree Code System Code

CODEX ALIMENTARIUS (GSFA)

INS-296